G. Ohloff, Fortschritte der chemischen Forschung (Advances in Chemical Research, Vol. 12/2, 201) reportedly states that macrocyclic carbonyl compounds having more than 13, but fewer than 19, carbon atoms are involved in achieving a musk odor. However, all commercial musk scents have ring sizes of 15, 16 or 17 carbon atoms. Extremely little is known about the olfactory properties of fourteen-membered ring ketones, and only then in isolated cases.
For example, Mookherjee, et al., U.S. Pat. No. 4,183,965 reportedly discloses the use of a mixture of 2- and 3-cyclotetradecen-1-one for reducing the bitter taste of foods. The compounds may also be used in perfumery and have a sweet, musk-like, exaltone-like, waxy, rooty odor.
JP-A 55-66534 reportedly discloses the synthesis of 5-cis-cyclotetradecen-1-one having a musk-like character by heating 1-vinyl-3-cis-cyclododecen-1-ol with an alkali metal or alkali metal hydride. E. Yoshi and S. Kimoto: Chem. Pharm. Bull 17, 629, 1969 and, subsequently, M. Karpf and A. S. Dreiding: Helvetica Chimica Acta, Vol. 58(8), 2409, 1975, reportedly disclose the synthesis of a mixture of cis- and trans -3-methylcyclotetradec-2-en-1-ones and 3-methylcyclotetradec-3-en-1-ones. Olfactory properties of these compounds are not given.
R. W. Thies and K. P. Daruwala: J. Org. Chem. 1987, 52, 3798 reportedly disclose the preparation of 3-methyl-trans-cyclopentadec-5-enone by treatment of trans- or cis-1-(1-propenyl)-trans-cyclotridec-3-en-1-ol with potassium hydride in hexamethylphosphoramide.
Demole, et al., U.S. Pat. No. 5,354,735 reportedly discloses cis- and transisomers of 3-methylcyclopentadec-5-en-1-one as scent constituents having musk-like properties. The cis-isomer is stronger, more elegant, and has more of a musk odor and less of an animal odor than the trans-isomer, which has more of a nitromusk character and ambrette seed odor.